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具有定制亲脂性的锰卟啉的设计与合成:氧化还原性质及超氧化物歧化酶活性研究

Design and synthesis of manganese porphyrins with tailored lipophilicity: investigation of redox properties and superoxide dismutase activity.

作者信息

Lahaye Dorothée, Muthukumaran Kannan, Hung Chen-Hsiung, Gryko Dorota, Rebouças Júlio S, Spasojević Ivan, Batinić-Haberle Ines, Lindsey Jonathan S

机构信息

Department of Chemistry, North Carolina State University, Raleigh, NC 27695, USA.

出版信息

Bioorg Med Chem. 2007 Nov 15;15(22):7066-86. doi: 10.1016/j.bmc.2007.07.015. Epub 2007 Aug 19.

Abstract

Thirteen new manganese porphyrins and two porphodimethenes bearing one to three different substituents at the meso positions in a variety of architectures have been synthesized. The substituents employed generally are (i) electron-withdrawing to tune the reduction potential to the desirable range (near +0.3V vs NHE), and/or (ii) lipophilic to target the interior of lipid bilayer membranes and/or the blood-brain barrier. The influence of the substituents on the Mn(III)/Mn(II) reduction potentials has been characterized, and the superoxide dismutase activity of the compounds has been examined.

摘要

已合成了13种新的锰卟啉和2种中位带有一至三个不同取代基、具有多种结构的二氢卟吩。所使用的取代基通常为:(i) 吸电子基团,用于将还原电位调节至理想范围(相对于标准氢电极接近+0.3V),和/或 (ii) 亲脂性基团,用于靶向脂质双分子层膜内部和/或血脑屏障。已表征了取代基对Mn(III)/Mn(II)还原电位的影响,并检测了这些化合物的超氧化物歧化酶活性。

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